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Issue 23, 2009
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Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation

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Abstract

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP.

Graphical abstract: Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation

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Supplementary files

Article information


Submitted
06 Jul 2009
Accepted
09 Sep 2009
First published
06 Oct 2009

Org. Biomol. Chem., 2009,7, 4960-4964
Article type
Paper

Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation

K. M. Allan, B. D. Hong and B. M. Stoltz, Org. Biomol. Chem., 2009, 7, 4960
DOI: 10.1039/B913336D

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